Reaktion #1435730

Reaktionsgleichung

hydrochloric acid

sodium hydride

ethyl 2-chloro-6-fluorophenylacetate

acetic anhydride

→

ethyl (2-chloro-6-fluorophenyl)acetoacetate

Ausbeute 35.8%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   Temperaturunder reflux
3. 3
   Temperaturrefluxed
4. 4
   Temperaturunder heating for 10 hours
5. 5
   TemperaturThe reaction mixture was cooled
6. 6
   Extraktionextracted with t-butyl methyl ether
7. 7
   WaschenThe organic layer was washed with dil. hydrochloric acid, aqueous saturated sodium bicarbonate solution, dil. hydrochloric acid and water
8. 8
   Trocknensubsequently, dried over sodium sulfate
9. 9
   Einengenconcentrated

Vorschrift

Into a mixture of 9.6 g of sodium hydride (60% in oil) and 200 ml of tetrahydrofuran, 21.7 g of ethyl 2-chloro-6-fluorophenylacetate were added dropwise under reflux. Then, a solution of 12.3 g of acetic anhydride in 40 ml tetrahydrofuran was added thereto and refluxed under heating for 10 hours. The reaction mixture was cooled, poured into iced dil. hydrochloric acid and extracted with t-butyl methyl ether. The organic layer was washed with dil. hydrochloric acid, aqueous saturated sodium bicarbonate solution, dil. hydrochloric acid and water, subsequently, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 9.27 g of ethyl (2-chloro-6-fluorophenyl)acetoacetate.

Quelle